ain't no fortunate son
by bananajelly
Summary: What if Dean was born as a girl? One-shots exploring the life and times of Deanna Winchester, and how things would have been different if it had been the Righteous Woman rather than the Righteous Man.
1. crossroads

**a/n:** these are all one-shots with no chronological order; they take place at various points though deanna's life, so you can pretty much read them any way you want. there won't be any wincest in this fic, possibly some destiel. this one contains spoilers for S2. hope you review!

* * *

The crossroads demon is a suit. He's the young professional type, dressed impeccably in dark gray with his patent-leather shoes polished to a reflective sheen. Handsome in a disaffected kind of way. The type of guy that Deanna would veer well away from normally, or maybe tug on his chain a bit if she's working a case. Except this is no human. This is a creature with eyes that flash glaring red underneath the weak light of the moon, who smiles at her like he wants to hurt her.

"Deanna Winchester," he says, words wrapping around her name like silk, "What a _treat_ it is to meet you. You know, I heard you were a pretty thing, but—" the demon steps in closer, his grin wide and predatory— "you're just _edible_."

She swallows the urge to throw an obscenity in his face.

"I'm not here to play games. I want you to bring him back."

"Big sister running to save little Sammy? I'm not surprised." His eyes shift back to a dark shade of brown, but nothing about his expression is remotely human. "Sorry, Deanna. No can do. I don't make deals with Winchesters."

"No," Deanna rasps out, grabbing the collar of his shirt to keep him from walking away. "No. You – you _need_ to bring him back. It's a fair deal. My soul for Sam's life. You collect in ten years."

The demon puts on a look of false contemplation for a few seconds. "Mm, tempting. But it's still a _no_ from me, sweetheart. Don't get me wrong—I'd love to get my hands on that soul of yours," he smirks at her, their faces only inches apart. "But ten years? Forget it."

"Nine."

"No."

"Eight."

"You're wasting my time here."

" _Five._ Five years or no deal." Her voice is cracking like ice underneath the weight of a heavy boot.

He looks at her, and does she imagine it, or does something like pity flit across his features? She tightens her hold on his collar, lowers her gaze to his jaw. His skin is smooth and unmarred, lips soft, probably belonging to some Wall Street intern who subsists off salads and vitamin water and free-range turkey. Is that a thing? Sam would know. _Sam_. God. Her throat constricts so tight she can't breathe, can't even think. Her eyes are wet and ready to spill. She can't live with it, doesn't want to live with it, this image of Sam's pallid body laid out on a table, stiff, unmoving, _cold_.

"Please," she says, and this time there is no pretense, only the raw echo of her grief.

"I can give you one year."

She doesn't have to think about it. Doesn't hesitate, not for a second. She crashes her lips to his, opening like a flower, her last defenses peeled away. The demon's lips are just as soft as they look. His hand comes to grip the back of her neck, tangling into the strands of her blonde hair oh-so-possessively.

When they break apart, his eyes are red again and the air is freezing, but Deanna doesn't care, nothing matters, nothing else matters but Sam, because he'll be back now, he'll be alive and breathing, he's her baby brother and he's _alive._


	2. growing pains

Deanna's used to pushing her baby brother around. She's used to having him look up to her, in a very literal sense. So she gets the shock of her life when Sammy comes barreling out of his bedroom one summer morning, his eyes all lit up.

"It's official," he proclaims, grinning so wide his mouth is probably going to fall off his face. "I'm taller than you, Dee." She raises an eyebrow at him, and insists they line up back-to-back before she can accept this new information.

He agrees enthusiastically. He's right – at age fifteen, Sam has shot right above her five-foot-eight stature, and it's not just the extra volume from his dark bangs. She knows, 'cause she smooths them down to check.

He is, unsurprisingly, way too happy about this revelation. "Now you can't call me 'midge' anymore," he says, arms crossed.

She ruffles his hair shamelessly. "You'll always be a midge in my eyes, midge."

But Sammy doesn't stop there. No, he just has to go ahead and shoot up an extra two, four, six inches (and counting), probably out of pure spite for her. Deanna does not take kindly to having to look up at him. "I'm telling ya, you've gotta be some kind of genetic freak, Sam," she says to him one day.

"Sorry, what? Couldn't hear you from up here." _He sure smiles a lot these days_ , she thinks grumpily.

And boy, does he use his new height to piss Deanna off in more ways than she'd thought possible. Sam's new favorite thing, apparently, is holding things just out of her reach. Deanna responds by coming up with new ways to bring him down a notch. When he tries holding one of her prized cassette tapes up over her head, demanding that they listen to something else than Metallica ( _anything else_ , _Dee, seriously_ ), she just leaps onto his back to make a grab for it. _That_ turns out to be an interesting game of keep-away.

When they fight, usually over the remote (Sam just happens to have the worst taste in television, ever) or some other stupid thing, she learns quickly that Sam has absolutely no qualms about playing dirty. He fights like a bitch. A ginormous bitch, but a bitch nonetheless, using his weight shamelessly against her smaller frame. She isn't sure whether to feel like a proud mom or an incredibly ticked off older sister.

The truth of it is, though, it's a little terrifying. Because her baby brother is growing up right before her eyes, and she can feel it in her chest, a wriggling worm of fear that tells her someday soon, she won't be able to protect him, not in the way she could when he was ten years old.

But for now, Deanna cracks jokes and learns a million new ways to call someone "sasquatch" and pushes that thought far, far away. She'll protect Sammy for as long as the world is turning, and then a little longer after that, and to hell if anything is going to stop her.

* * *

 **author's note:** All this is just my super self indulgent AU, honestly. reviews are greatly appreciated! I plan to write a lot more of these.


	3. birds and the bees

**author's note:** these are getting progressively more lighthearted, what's happening

* * *

The guy she brings home from the bar – David? Daniel? – isn't exactly prince charming, but he's got nice, broad shoulders and strong arms, and that's good enough for a Thursday night. Dad is off on a hunt two states over, so she lets herself loose, gets so plastered that she forgets Sammy is still home.

So there she is, dry-humping a stranger on their ratty couch while he's fumbling with her bra. She hasn't gotten laid in too long, and now she's practically boiling over with pent-up lust, needy and hot and desperate. David/Daniel manages to unclasp the bra and his hands move to her waist while she slides the garment off. The air is cool against her bare skin, and she wraps herself around the warm body before her, about to tug his boxers off when her fifteen-year-old brother walks in from the other room, clad in his pajama shirt and sweatpants.

"Oh my god, Dee!" he yells, raising a hand to shield his eyes. And then, as if realizing the presence of David/Daniel, he exclaims, "that's my _sister!_ " He sounds so deeply offended that it'd be hilarious if it were any other situation.

"Sammy, get the hell out!" she shouts, scrambling off the guy in an ungraceful tangle of limbs. Needing no more instruction, Sam darts back through the door.

"Woah," the guy asks, completely taken aback. "Who's the kid? We can go back to my place if you've got company –"

But no, the moment is _beyond_ lost, and Deanna shakes her head. " _That_ was my little bro. Kind of puts a damper on the mood." When the guy doesn't budge, she raises an eyebrow pointledly and tosses him his discarded jeans. "Uh, you can see yourself out."

The guy's expression quickly goes from expectant to pissed, and he grumbles something about blue balls, but Deanna manages to usher him out without much more fuss. Once he's gone, she dons her shirt and shorts once again, not bothering with the bra – it was a push-up anyways.

"You decent?" Sam yells from the other room, louder than he needs to, and she can hear the embarrassed pitch to his voice.

"Yeah," she replies, scratching at her neck uncomfortably. She feels a vague sense of guilt. Her brother is fifteen, and she was already well-versed in the art of knocking boots at his age, but, damn, this is _Sammy_ , whose first instinct in every new town is to register for a card at the local library. There's just no way he's been getting any. She hopes she didn't traumatize him or anything.

"Jesus, Dee," he says, walking back in. His look of pure trauma has been replaced by Bitchface #4. "Could you find a motel next time? It's a _school night_."

She decides to play it off as a joke. That always works. "You see, when a guy and a girl love each other very much –"

"Oh god, stop."

Bitchface #5 is revving up. She smirks.

"People get urges! I don't know about you, but if mine aren't relieved every once in a while, then, you know…" Deanna makes a vague gesturing motion at her pelvis. "It gets all backed up. It's not pretty."

Sam is now burying his face in his hands. "That's wrong on so many levels."

She fake-sighs. "Okay, I am sorry you had to see that, Sammy. Although, hey-" she can't stop the smile from spreading across her face. "Now you can tell all your buddies you've seen a girl topless, huh?"

"DEE."


	4. kiss

Deanna's thirteen when she asks permission to go over to Eric Conyers' house, and from the look on dad's face, she thinks he'll combust into flames right then and there. He tells her that Eric can come visit _her_ , _and only when I'm home, young lady, and don't let me catch you sneaking around, you understand?_ Her response is an earnest _yessir_ as always, even as the sinking feeling takes over her stomach. She can't explain to dad that there's no way in hell she's inviting Eric over. He'd probably never want to talk to her again after seeing the state of their crappy motel room, especially with her little dork brother running all over the place and demanding they watch National Geographic.

For one of the first times in her life, she isn't an obedient daughter, and sneaks out on a rare night when dad and Sammy are both at home, with dad passed out on the couch with his arm in a sling, and Sammy asleep in their room. She meets up with Eric at the local diner, and can't stop herself from ogling his dark, chocolaty eyes and easy smile. He pays for their cheeseburgers and shakes, and talks to Deanna like she's _normal -_ like she's one of the girls from school who wears cute clothes and butterfly clips and doesn't have band aids covering thirty percent of her body. She really likes the way he stares at her blonde hair, and learns to flip it over her shoulder every few minutes or so. At the end of their dinner date, she thinks she's a little bit in love, and they end up sharing a clumsy kiss in the parking lot before he waves her goodbye.

The next day, dad's arm is still busted up pretty badly, and she stays home from school to help him parse the details of a potential case. She only leaves to pick Sammy up, and when she comes back, her father is standing there, stony-faced.

"You got a call," he says.

Her stomach flips pleasantly before it's replaced by dread. "I did?"

"That Eric kid. You went out to see him, Deanna?"

"We - we just went out for dinner." Her voice sounds as small as she feels. Dad stares at her, and right then she knows it doesn't matter what she did - it matters that she disobeyed his orders. It's startling to realize how fiercely she hates herself for that.

"Dinner," he echoes. "And you thought _dinner_ was more important than watching out for your brother?"

Sam is standing there, his gaze flicking between him, the beginnings of protective anger forming on his face. She knows he'll stick up for her, but she doesn't want him here for this. "Sam, go to your room," she orders him.

She endures the yelling stoically, of course she does, and when he's picked up a new case the following week and they're back on the road, she doesn't say a word about not seeing Eric again.


	5. the things we keep quiet

a/n: warning for attempted sexual assault, and language. this chapter is quite dark, so please read at your discretion!

* * *

She's so stupid, should've seen this coming, should never have taken the shortcut back to the motel room, not on a night like this. Not when she's past the point of _buzzed_ and well into _shitty-hangover-tomorrow_ territory, and she's wearing these stupid fucking heels instead of her combat boots with the knife tucked in the heel.

Not when Dad is hunting down a vampire nest in Kentucky, and, god, if she can't fight her attacker off – and that's looking like a very real possibility, given that the piece of shit has at least six inches on her and solid, brutal strength – _Dad can't know._

He's the dickwad who grabbed her ass in the bar, she realizes, recognizing his features even in the darkness of the alleyway. Deanna had whipped around like a wildcat and punched him hard on the left side of his jaw, relishing in the solid hit, and she can see the bruise blooming there now. She thought that had been the last of it.

But no, he'd pounced on her once she was far enough from the bar, grabbing her long hair from behind and repaying her with two hard punches to the sides. Now he's got her pinned to the wall with a thick arm pressed up against her neck, hot, sour breath washing over her face. Deanna flails desperately beneath him, her movements quick and jerky as her air supply dwindles, and she tries to aim her knee for his groin, but his leg comes smashing down on hers and she has to bite down a scream. His other arm comes up to grope hungrily at her chest, tearing down her shirt to expose her bra.

"Little tease," he breathes at her, and she's sickened by how she can feel the lecherous rumble of his voice through his chest. His arm loosens oh-so-slightly, just enough so that she can wheeze down enough air to keep from passing out before he presses it tighter again, but _fuck_ , her mind is all soppy with alcohol, and world is tilting on its axis around her, making her vision go spotty at the edges. "Just asking for it back there, weren't you? Well," he crows, hand pulling down her denim skirt, "I'm gonna give it you, darlin'."

 _Fight, Deanna, fight,_ begs a voice at the back of her mind, and she tries again to recall a million hours of training and sparring and practice. But the night is spinning, and the asshole's compressing her throat, choking the breath out of her, and her limbs are about as efficient as pulverized jello.

She closes her eyes to keep the tears at bay, half out of pain and half out of sheer, uncontrolled panic, and suddenly— the weight is gone, pulled right off of her, and nothing has ever felt better than this utter lightness. She half-slides down the wall, taking in huge, desperate gulps of breath, and only registers her savior a second later.

Somehow _Sam_ has found her, run into the mouth of the alleyway, and holy shit, he's fucking _furious._ He's grabbed the guy by the shirt and thrown him into the opposite wall, a fist coming down onto the asshole's face, and Deanna is scared by Sam's expression.

"Sam," she croaks, and either he doesn't hear her or he doesn't care. She watches for a moment longer, in amazement as her seventeen-year-old brother takes on this trucker and seems to be winning. The asshole shoves back at Sam and throws a punch, but Sam dodges it easily before landing a hit that looks like it knocks out a few teeth.

Suddenly, it's like the sounds of flesh-on-flesh contact and pained grunting have reached her brain, and _DEFCON 1_ sirens go blaring in Deanna's head: _Sam's in trouble, you stupid shit, DO SOMETHING._ She scrambles to her feet, not even noticing the pain flashing along her sides and her leg, and lunges at the guy.

Turns out, though, Sam doesn't need her help, and she is hardly at the top of her game right now. Sam slams the asshole's head into the unforgiving brick wall, and his unconscious body slumps to the ground, mouth all bloodied and lip split wide open. Sam is— Sam is gigantic, chest heaving, and where the hell did her skinny shrimp of a brother go?

Then he turns to her, takes in her ripped shirt and battered appearance. "Dee," he chokes out. "Are—are you okay?" He steps closer to her, eyes full of lingering anger and concern.

"I'm just peachy," she says hoarsely, then clears her throat. " _Peachy_." And then Sam's gathering her up in his huge arms, with her burying her face into the material of his shirt, and this isn't how anything is supposed to go at all. Sam isn't supposed to rescue her, he's not supposed to be the one who swoops in all heroic-like and pummels the crap out of her attacker. _She_ looks out for _him_ , not the other way around, and the realization of what would've happened without his intervention is a shard of ice in her heart.

But right now she is so, so relieved, and she lets Sam hold her, his hands circling her back. She feels the tension of his body, like his anger is still barely contained underneath his skin.

"I got worried," he says to the top of her head in a tight voice. "You weren't back and I got worried. Thank _fucking_ god I did. That guy, he…" Sam trails off for a moment, and she can't see his face, but she knows that he's looking at the crumpled form on the ground. "He was going to—"

"No, he wasn't," she mumbles into his shirt. Sam wasn't asking a question, but things have slipped too far out of her control, and the denial is almost instinctive. He stiffens even further at the lie.

They leave after Deanna lands a hard, angry kick to the asshole's chest, and she hopes that was a snap of a rib she heard. Sam looks like he wants to do more, but she doesn't let him. Two hours later, they're back at their motel room of the month, and Sam hasn't stopped hovering over her for one moment, fuming not-so-quietly. "And where's Dad, huh?" he spits out violently. Deanna sits on the bed and shakes her head of freshly showered hair. "It's his goddamn fault. Leaving us here alone, all the time, when anything could happen, and look at what _did_ happen."

"I'm twenty-one years old, Sam." She hasn't stopped trembling quite yet, but she is hyper-aware of the delicacy of this situation. There's an impending freak-out coming, another week of shouting matches between Sam and Dad. Deanna has to stop it before it starts.

"Off on his stupid _hunt_ , doesn't give a shit about his own daughter—"

" _Sam_ ," she says, using her big-sister voice, and at last he's listening to her. "You're not gonna breath a word of this to Dad. I mean it. Not a word."

He looks like he's gotten a spontaneous case of lockjaw. "No fucking way."

"Yes fucking way. He's got enough on his plate, alright? I'm not gonna have him half of out his mind trying to get his hands on this guy. You and I already beat him down pretty good."

Sam's all hot-eyed as he says, "Do you hear yourself, Deanna? Do you even care about yourself? Because guess what, I do! You can't just sweep this under the rug! If I hadn't found you in time…"

"Then I would have _handled it_ ," she lies through her teeth. "Really, Sam, he got the jump on me. I could've turned it around." Maybe she can make him believe it, too, restore some semblance of balance and keep it all from crashing down.

At this, Sam looks incredulous. "Are you serious? You could barely _stand_. You're not hiding this from Dad."

"Yes, I am, and you're going to shut up about it too, because I'm the older one, and you have to listen to me." Sam's about to open his mouth to protest, so she carries on, softer this time. "Please, Sam. Just… do this for me. Okay?"

He stares at her for a long moment, saying nothing, and storms into the bathroom. She closes her eyes and tucks her chin to her knees. Panic flickers faintly in her chest, but there's not much more she can do, and she's hinging on her trust in Sam, that he'll listen to her when it matters most. Things are barely holding together as it is, and even then only through Deanna's sheer perseverance, this life as a Winchester human buffer. For it to work, Dad can't know about any of it. She needs to be his solider, his rock to lean on.

John Winchester comes back home to his children two days later, and he is none the wiser.


	6. like mary

**a/n:** takes place pre-series. the relationship between girl!dean and john is pretty fascinating to me.

* * *

John trains the arrogance out of her; he tells her, in no unclear terms, why she has to be more prepared than Sam. She learns how to use her size to her advantage, how to land a kick to the groin with maximum efficiency. John shows her how to use agility first, and punches second. By the time she hits high school, she's able to take down guys twice her size.

But even after everything, all the paramilitary training and shooting practice, she knows that there's a lingering thought in Dad's mind. The hunt would be easier if she were a boy. There are other dangers for her, things that Dad wouldn't have to worry about if she wasn't a pretty girl, albeit a pretty girl with muscle in her limbs and a backbone of steel.

It's something that they never talk about, except for the days when John gets drunk out of his mind. He'll come home sometimes with his breath stinking of whiskey, the circles under his eyes looking more sunken than ever. When Sam was younger, he'd be clucking with worry, asking her if he'd be alright, but these days he just scoffs at the sight of his father.

She doesn't like seeing Dad that way. It's like losing the very footing that she stands on. On those occasions, it's up to her to peel the leather jacket from his shoulders, take his boots off and lug him onto the bed. Sometimes he'll drift into sleep the second his back hits the mattress; other times, he'll talk to her, his words slurring into each other.

 _Worried for you, Dee. You know that? Real worried._

 _Yeah. I know, dad. It's okay. You go to sleep now._

 _God, you – you look just like her._

 _Dad-_

 _You look like Mary._

Deanna freezes at that, feeling something cold washing over her skin, and swallows down a lump in her throat. It's not like she hasn't noticed the resemblance. It's the reason Deanna doesn't like looking in mirrors, why she lines her eyes in smudgy black kohl and opts for denim and flannel over blouses and skirts. Sometimes all she can see in her own reflection is her mother's face: her freckled complexion, her green eyes, the slim lines of her jaw. If that's what it's like for her, then she can't imagine what it's like for Dad.

She understands, then. It's not just that hunting would be easier if she were a boy. Everything would.


	7. castiel

**author's note:** takes place in early season 4. this series will still mainly focus on the Winchesters, but a little Castiel never hurt anyone :)

* * *

Deanna doesn't like not knowing what to make of Castiel. She almost wishes he would mess up, do something unforgivable, let her know once and for all where he stands. He's an _angel_ , for god's sake (or whoever the hell she's supposed to pray to these days, because evidently, God is never going to cut her a break). It's still hard to wrap her mind around, even in the midst of all the rescued-from-hell crap, and it doesn't help that she's got nobody to talk to. Bobby's got his own worries, and Sam is a million miles away, off chasing his pet demon whenever she turns her back. She's just tired of it all. Cas—and the fact that she's calling him _Cas_ should be a red flag on its own, damnit—looms over it all, inexplicable and impossible and hypercharging the air with a kind of energy she can almost _taste_.

If Deanna ever believed in angels... well, she wouldn't picture them like Cas. He's almost human in his civilian meatsuit. Almost. There's something mystical about him. That should be rich, coming from the girl who deals with the supernatural on a 24/7 basis, but this is a different kind of mysticism altogether. In her rather extensive experience, _arcane_ usually goes hand-in-hand with _malevolent/wants-to-kill-you-or-your-brother._

But the angel is frustratingly _not-malevolent,_ and he's got eyes that make Deanna wonder if the underbelly of the earth isn't going to swallow her whole again, that maybe she isn't destined to be shredded apart and put back together for the rest of eternity.

It's hard to admit to herself that she wants to trust him. It's a leap that she's terrified to take, and maybe that's why she's half-hoping he'll betray them before she has the chance. People that Deanna Winchester trusts end up dead or gone or in cahoots with a black-eyed bitch. But that can't happen with Castiel, apparently, as he's much too powerful to get himself ganked and much too solemn to hook up with a demon.

That leaves _gone_.

Deanna curses herself. Whether Cas is on their side or not, she's not going to get attached to his feathery ass, that's for sure. Well. That's the plan.


	8. mean girls

**author's note:** high school aged deanna, middle school aged sam. i imagine dee wouldn't have had the best HS experience. by the way, if you're enjoying the story, then please review! it's great to get views and all but really, i want to know what you guys think :) do you have headcanons for deanna? are you a fan of her characterizaton here? lemme know!

* * *

Most of the shit Deanna deals with is water off a duck's back. She kills _monsters_. She can deal with girls who think they're better than her because they wear Juicy Couture and sport French manicures instead of chipped black polish. She knows their type all too well: girls who make the cheerleading team and go to church on Sundays and whisper to each other, _that Winchester girl, I heard she puts out to any guy who wants it._

But some of it sticks. There'd been Jenna Platts, for one, who'd spread rumors about how Deanna was a dyke who'd sleep with anything that moved, including the substitute teacher. Nothing particularly innovative there. The problem was, though, that the bitch brought Sam into it. He started hearing about it at school from dickheads who thought he'd be an easy target, and _that_ was crossing a line. Outside of tailing Sam to all his classes (which she considered), there wasn't much she could do to help him, so she took it on Jenna's pretty new car, carving pentagrams into the Audi that Mr. and Mrs. Platts had bought her for her sixteenth.

Marjorie Chapman was another one for the books. Deanna knew Marjorie had hated her guts from the moment she saw her. Hated her too-tight denim skirt and raggedy band tees and the effortless way she had with boys, how she'd be able to pull them in with a smirk.

In Deanna's defense, she did _not_ know it was Marjorie's boyfriend.

She remembers how the girl had sneered at her and said, _I don't even want to know whatever it is your daddy did to you that made you this desperate._ Deanna broke her nose swiftly afterwards. It'd been pure instinct, a white-hot flash of rage that sent her fist flying into Marjorie's smug face. Marjorie hadn't even tried to fight back. She'd just screamed and clutched at her face till the teachers rushed in and started acting like Deanna had shot the queen or something. Deanna didn't regret any of it, except when Dad found out she'd been expelled.

Still. Most of it makes her want to laugh more than it makes her want to cry. The way the girls at school look at her, you'd think Dee was a goddamn murderer or something. "Fuck 'em," she says to Sam. "See, I'm too hot for my own good, little brother. Everyone either wants to kill you or kiss you. Good thing you'll never have to worry about that,"

"Your modesty's really your best feature." Sam hardly looks up from his algebra homework.

Deanna thwaps him on the head before going in with another coat of black nail polish. "All my features are my best features."


End file.
